Cost of breaking in this Galloway? Is it Necessary?

At this point I would get a trainer and see how they handle the problems. Make sure you can visit the horse after a couple weeks, and watch the trainer ride him so you can see what may need to be done when you get home. Maybe take a few lessons on your horse, or take lessons on one of theirs while they are riding yours. That way, you will know what to expect and also get to know how the trainer corrects it.